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Natural deep eutectic solvents as an efficient and reusable active system for the Nazarov cyclization

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Abstract

Natural deep eutectic solvents have emerged as alternative non-toxic, non-aqueous solvents for an increasing number of synthetic transformations. Remarkably, in some cases one (or more) components of the NaDES plays an active role in the reaction mechanism and directly participates as either a catalyst or a reagent in the reaction. In this paper, we tested several NaDESs in which one of the components is a carboxylic acid as a medium to perform the Nazarov cyclization of divinyl ketones to obtain cyclopentenones, a widespread motif in natural compounds. The reaction conditions were optimized and the scope was investigated on C-, O- and N-derived compounds. To assess the full sustainability of the proposed approach, the recyclability and scalability of the process were investigated, thus proving that multi-gram preparations are possible with complete recycling of the medium.

Graphical abstract: Natural deep eutectic solvents as an efficient and reusable active system for the Nazarov cyclization

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Publication details

The article was received on 07 Oct 2019, accepted on 19 Nov 2019 and first published on 19 Nov 2019


Article type: Paper
DOI: 10.1039/C9GC03465J
Green Chem., 2019, Advance Article

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    Natural deep eutectic solvents as an efficient and reusable active system for the Nazarov cyclization

    S. Nejrotti, M. Iannicelli, S. S. Jamil, D. Arnodo, M. Blangetti and C. Prandi, Green Chem., 2019, Advance Article , DOI: 10.1039/C9GC03465J

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